3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Name:3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:627860-02-0
Molecular Formula:C₃₈H₆₅NO₆Si₃
Molecular Weight:716.194
Hs Code.:

3,4-bis-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-pyrrolidine-1-carboxylic acid <i>tert</i>-butyl ester

Synonyms:3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of 3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of 3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 8 articles about 3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

: 627860-01-9
3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 627860-02-0
3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; at -78 ℃; for 0.25h;
DOI:10.1016/j.tetlet.2003.08.030

Reference yield:

: 290354-66-4
(2S)-3-(tert-Butyldiphenylsiloxy)-2-(dibenzylamino)propanal

: 627860-02-0
3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: iPr₂NEt; n-Bu₂BOTf / diethyl ether / 1.5 h / -78 °C

1.2: 75 percent / diethyl ether / 2 h / -78 - 0 °C

2.1: Me₃Al / tetrahydrofuran / -30 °C

2.2: 91 percent / tetrahydrofuran / 18 h / -30 - 20 °C

3.1: 71 percent / H₂ / Pd(OH)2 / methanol / 72 h / 20 °C

4.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 20 °C

5.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 20 °C

6.1: 96 percent / LiEt₃BH / tetrahydrofuran / 0.25 h / -78 °C

With 2,6-dimethylpyridine; dmap; di-n-butylboryl trifluoromethanesulfonate; hydrogen; trimethylaluminum; lithium triethylborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1016/j.tetlet.2003.08.030

Reference yield:

: 290354-72-2
(2S,3R,4R)-2-Benzyloxy-5-(tert-butyldiphenylsiloxy)-4-dibenzylamino-3-hydroxy-N-methoxy-N-methylpentanamide

: 627860-02-0
3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / H₂ / Pd(OH)2 / methanol / 72 h / 20 °C

2: 85 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 20 °C

3: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 20 °C

4: 96 percent / LiEt₃BH / tetrahydrofuran / 0.25 h / -78 °C

With 2,6-dimethylpyridine; dmap; hydrogen; lithium triethylborohydride; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tetlet.2003.08.030